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Toward the Development of a General Chiral Auxiliary. A Total Synthesis of (+)-Tetronolide via a Tandem Ketene-Trapping [4 + 2] Cycloaddition Strategy

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Contribution from the Department of Chemistry, University of Rochester, P.O. Box 270216, Hutchison Hall, Rochester, New York 14627-0216
Cite this: J. Am. Chem. Soc. 2006, 128, 32, 10572–10588
Publication Date (Web):July 21, 2006
https://doi.org/10.1021/ja0581346
Copyright © 2006 American Chemical Society
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    Abstract

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    A highly convergent, enantioselective total synthesis of the aglycone of the tetrocarcins, (+)-tetronolide, is described. The synthesis highlights the use of several new methods, including camphor auxiliary-directed asymmetric alkylation and the enantioselective preparation of acyclic mixed acetals bearing chirality at the acetal center, and the highly efficient connection of the two major precursors via a ketene-trapping/intramolecular [4 + 2] cycloaddition strategy.

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    Experimental procedures for numbered intermediates 9, 12, 13, 16−19, 29−31, 33, 34, 36−39, and 41 along with unnumbered isolated intermediates. Copies of 1H NMR and most IR spectra for numbered intermediates 5−7, 9,12−14, 16−19, 21, 23−26, 28−34, 36−39, 41, 43, 45, 47, 50, 51, 53, and 54 and unnumbered isolated intermediates; 1H NMR spectra of our synthetic, Yoshii's synthetic, and natural tetronolide (+)-1, and X-ray crystallographic data for diol 46. This material is available free of charge via the Internet at http://pubs.acs.org.

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